Acetic Acid → HCID 11841701, compound

HRID 904822Notes

Reaction equation

HRID 904822 reaction equation
[C:1]([NH:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15])(=[O:3])[CH3:2].[BH4-].[Na+].C(O)(=O)C>C(O)C>[C:1]([NH:4][C@@H:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C@H:6]1[OH:15])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 9859076HCID 9859076, compound

Product 1

HCID 11841701HCID 11841701, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the 2-acetamido-3,4-dihydronaphthalen-1(2H)-one from Step A in absolute ethanol (150 ml) was added sodium borohydride (2.0 gms, 0.05 m) in portions. The reaction mixture was stirred at room temperature for 1/2 hour. Acetic acid was added dropwise to destroy the excess sodium borohydride. The reaction mixture was poured into water and extracted with ethyl acetate (3×150 ml). The ethyl acetate was washed with saturated aqueous sodium chloride (150 ml) and dried over anhydrous sodium sulfate. After filtration the solvent was removed under reduced pressure to yield 5.5 gms (54%, over Steps A and B), of product as a solid.

Workup

  1. customto destroy the excess sodium borohydride
  2. additionThe reaction mixture was poured into water
  3. extractionextracted with ethyl acetate (3×150 ml)
  4. washThe ethyl acetate was washed with saturated aqueous sodium chloride (150 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration the solvent
  7. customwas removed under reduced pressure
  8. customto yield 5.5 gms (54%, over Steps A and B)

Sources & evidence

ORD record
ord-be04bfdb20004457acb2cd6e96904541
Source dataset
uspto-grants-1983_12
Patent number
US04420480

Reaction notes

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